Toronto Maple Leafs playoff picture: How Auston Matthews and co's post-season chances look like before taking on Boston Bruins

The Toronto Maple Leafs haven't won the Stanley Cup since 1967, when they won the last championship of the Original Six era. Since expansion, the team hasn't even returned to the Stanley Cup Final. Since 1993, Toronto hasn't played in the conference final, missing out on decades of championship opportunities.

Now, with one of the NHL's most lethal cores, led by 54-goal scorer Auston Matthews, 80-point player William Nylander and All-Star Mitch Marner, the Maple Leafs are positioning themselves for a deeper run than the second round in 2023.

Toronto Maple Leafs

According to MoneyPuck.com, the team has a 99.7% chance of making the playoffs and an 8.2% chance of winning the Stanley Cup. However, they are on pace to play the Boston Bruins in the opening round.

Since expansion, the Maple Leafs have had no luck against its Original Six rivals, going 0-6 in playoff matchups since 1959, the last time they eliminated Boston in postseason action.

Although every year may differ, Toronto almost always has the same playoff results. Since 2000, the Maple Leafs have been 47-57, with a 1-8 record in Game 7s. Overall, they have been 47-52-12 against Boston in the regular season for the past 24 years.

Despite their playoff misery at the hands of the Bruins, fate always has a way of stepping in. For 86 years, the Boston Red Sox didn't win a World Series, coming close on several occasions, until "The Curse of the Bambino" would get into their heads, and the team would lose.

However, in 2004, the Red Sox overcame the professional sport's greatest deficit, a 3-0 series lead, beating the New York Yankees en route to a World Series title. Interestingly, the Maple Leafs have the same problem in playing against the Bruins and could finally have the lineup to overcome their past failures.

If Toronto meets Boston in the opening round, it would be a playoff series for the ages, with the odds in the Canadian team's favor for once.

Is this the year for Toronto Maple Leafs to overcome playoff failures and win the Stanley Cup?

On Monday night, the Bruins rolled into Scotiabank Arena and steamrolled the Maple Leafs in front of their hometown fans with a 4-1 win. On Thursday, the two meet again in Boston, with Toronto gearing up to avenge their latest loss while winning against their divisional foe for the first time in 2023-24.

After 62 games, the Maple Leafs have accumulated 80 points, seven behind the Bruins, who rank second in the Atlantic Division. Both clubs are chasing the Florida Panthers, who have 90 points in 63 games. Although winning the division may be a long shot, overtaking Boston and gaining home-ice advantage in the opening round isn't out of the question.

Right now, the Bruins are scrambling for wins and points, with eight of their past 12 games requiring extra time and the team just collecting a 4-2-6 record. They have struggled on the back end since Hampus Lindholm went down with an injury on Feb. 19, getting outscored 30-28 by opponents.

Meanwhile, the Maple Leafs are one of the hottest teams in the NHL, with a 10-2-0 record in the past 12 games, beating their opponents by a 51-33 margin. They are getting outstanding goaltending from Ilya Samsonov, who is 11-3-0 with a .909 save percentage since returning from the minors on Jan. 14.

Matthews is on pace for 70 goals, Nylander could collect his first 100-point campaign, Marner could reach the century mark for the first time in his career, and captain John Tavares is about to hit 20 goals for the 14th time in his career.

Even though Toronto looks like they are firing on all cylinders, there are still some lingering questions ahead of the NHL trade deadline, which they began to address with the recent acquisition of Ilya Lyubushkin and Joel Edmundson.

If general manager Brad Treliving wants to ensure playoff success, he'll tinker with the lineup once more to give his lineup the best opportunity to win more than a couple of games in late April.

Tonight's matchup against the Bruins isn't a must-win, but it would help get them two points closer to a higher seed and a favorable spot in the postseason. However, if they want to begin the mental process of burying any lingering doubts about their playoff capabilities against Boston, this contest would be one step in that direction, especially if they win big on the road.